25 Smoothest Bourbon Whiskeys Of All Time

Bourbon is a distinct, American version of whiskey notable for its saturated amber color and layers of oaky, vanilla, caramel, and fruity tastes. Although it takes a lot of skill, expertise, and patience to craft the perfect draught of bourbon, the ingredients are really up to the distillery. Some whimsical distillers will go for decidedly unconventional elements, lovingly lacing their bourbon with bright wintergreen notes, hints of tropical fruits, or unexpected florals.

Others prefer to pay homage to tradition, leaning hard into creamy vanilla, decadent caramel, and toffee for that coveted bourbon roundness that true aficionados love and crave. Whether you're looking for a unique twist or a perfectly distilled, aged, and flavored rendition of this classic spirit, you're in luck. There are plenty of distilleries across the United States that feature incredible bourbons for every taste and price range. 

Here's a look into 25 of the smoothest bourbon whiskeys available. Sip 'em straight, on the rocks, or stirred into an Old Fashioned, but do add these fantastic bourbons to your home bar, stat!  

Heaven Hill's Heritage Collection 17-Year-Old Barrel-Proof Bourbon

Kentucky's Heaven Hill Distillery produces some lip-smacking fine bourbons, but none quite rivals its Heritage Collection 17-Year-Old-Barrel-Proof. This exceptional draught features a unique mash bill (via Heaven Hill) and is a tantalizing, stately bourbon with layers upon layers of rich flavors. You'll notice the aroma first; a heady blend of rich stone fruit shot through with bright apple and rich chocolate. The first sip is full of whimsical surprises, like fresh strawberry and toasty cereal (via Bourbon Banter).

It's a bourbon lover's bourbon, laced with rich bready notes and plenty of sumptuous chocolate. Yet, despite the bevy of robust flavors, Heaven Hill's Heritage Collection 17-Year-Old-Barrel-Proof never tastes cluttered or overwhelming. Instead, each different note shines beautifully in a rich interplay of sweet fruit and delicious chocolate. Drink it with a tiny drop of water to open things up, or enjoy it neat in a rocks glass.

Stillhouse Black Bourbon

Stillhouse hails from Tennessee, and like many exceptional southern bourbon distillers, its products are smooth and endlessly drinkable. Two things that set Stillhouse Black Bourbon in a celebrated category all of its own are the innovative packaging and decadent coffee flavor that permeate each sip. If you're looking for a different spin on your standard bourbon, this is it. Stillhouse Black Bourbon has a fresh coffee nose, interspersed with notes of oak and a touch of rye.

The taste is clean and distinctive, with plenty of rye and deep woody flavor. You'll also get a bit of caramel on the back-end, a sweet surprise that perfectly rounds off this fantastic drink. According to Field Magazine, Stillhouse is the distillery of choice for hikers who love their bourbon, thanks to the indestructible packaging. Stillhouse is also the Official Bourbon of the Daytona 500 (via Daytona International Speedway). So whether you enjoy this bourbon as a sippin' drink or stirred into a mint julep, get your hands on some Stillhouse goodness.

High West American Prairie Bourbon

Utah might not be as famous for its bourbons as the whiskey-drenched southern states, but Park City boasts one of the country's top distilleries: High West. High West American Prairie Bourbon comes in a sleek, handsome bottle with an old-timey flair that's been double barrel-aged and full of a joyous blend of sweet and cereal-based flavors (via Virginia Alcoholic Beverage Control Authority). You'll find lovely, sugary surprises like honey, vanilla, and even luxe caramel apple. On the bready side, expect deep notes of cornbread and oats.

Since this bourbon was aged in Madeira casks, savvy drinkers might even catch a touch of wine lingering on the back-end of their sip, according to Virginia Alcoholic Beverage Control Authority. Although this bourbon is undeniably sophisticated, its delicate sugar-based notes make it accessible to both seasoned bourbon drinkers and newbies. It's an ideal gift for discerning tastes and a great way to introduce bourbon novices to the drink.

Frey Ranch Single Barrel Straight Bourbon Whiskey

Nevada's Frey Ranch specializes in single barrel offerings with sleek characteristics, which is why its Single Barrel Straight Bourbon Whiskey is a straightforward and perfectly executed salute to bourbon. According to Whiskey Consensus, these delicious draughts get you with a smooth hint of custard, rich spices, stone fruit, and honey from the first sniff — and it only gets more nuanced and exciting from there.

Expect a symphony of different exquisite notes, like rich chocolate, a hint of coffee, fresh maple syrup, and a little cherry Dr. Pepper. There's even more cherry waiting for you inside the glass, balanced expertly with oak and warm cinnamon. One of the most exciting things about Frey Ranch's Single Barrel Straight Bourbon Whiskey is that the flavors wouldn't seem to work together — yet they do — proving once and for all that it's not just the south that makes a mean bourbon.

Heaven's Door Bootleg Series

Head to Nashville, and you might find yourself knocking on Heaven's Door distillery to sample some of the best bourbons in the state (via Men's Journal). According to Breaking Bourbon, this bourbon has rock 'n roll roots as it's the brainchild of Bob Dylan. Heaven's Door Bootleg Series comes in gorgeous bottles featuring "Sunday Afternoon," Bob Dylan's striking painting of the American southwest. In addition to the beautiful bottles, the Heaven's Door Bootleg Series has some pure gold inside.

This award-winning bourbon (via PR Newswire) is tinged with warm brown sugar, chocolate, and plenty of range — with a light but perceptible ribbon of spice running through every sip. You'll get rich leather, spicy peppercorn, and full-bodied oak at the beginning, with a touch of honey and orange at the end. A beautiful, artfully orchestrated bourbon, Heaven's Door Bootleg Series is a masterpiece that bourbon enthusiasts will love.

Angel's Envy Cask Strength Bourbon

Angel's Envy Cask Strength Bourbon is a bold, robust drink with plenty of deep port wine notes. The port wine lends a mature and chic edge to the bourbon, and you can tell that it's spent a good, long time in the port wine barrels. Kentucky-based Angel's Envy Distillery is no stranger to putting out incredible, complex bourbons. Still, Angel's Envy Cast Strength Bourbon is a cut above, with luxe touches of honey, cherry, fresh peach, and warm brandy (via Lane Report).

In addition to the stone fruit and honey, you'll get creamy vanilla, oak, and sophisticated leather. Angel's Envy works with a light hand, blending all of these disparate notes together in a lovely tapestry that's approachable enough for new bourbon drinkers to enjoy while still providing deep elements of flavor that connoisseurs will pick up on. So whether you sip it straight, on the rocks, or pair it with your favorite cut of steak, do get your hands on a bottle of Angel's Envy Cask Strength Bourbon.

Four Roses Al Young 50th Anniversary Small Batch Bourbon

With a stately, old-school bottle, and a whole heck of a lot of yumminess inside, Four Roses Al Young 50th Anniversary Small Batch Bourbon is a true home-run in any bourbon lover's book. Hailing from Lawrenceburg, Kentucky, Four Roses' premium blend leans heavily into sweet territory, and it works beautifully. Bring a brimming rocks glass of this special anniversary blend to your nose, and you'll be transported straight to your childhood summer with gorgeous honeysuckle and sugary caramel notes (via The Whiskey Wash). 

The first sip is packed with pleasant surprises, from ripe summery fruits like apricots and peach, then a subtle note to sweater weather with figs, vanilla, and woodiness. It's a joyful blend that finishes with a surprising hit of fresh mint. Four Roses Al Young 50th Anniversary Small Batch Bourbon is one of the rarest bourbons in the world — but if bourbon is your thing, it's totally worth the investment.

Great Jones Distilling Company Straight Bourbon

According to Yahoo! Life, Manhattan-based Great Jones Distilling Company is a craft distillery right in the heart of the Big Apple, and it brings 11 generations of experience to the table. New to the scene, but undeniably a heavyweight, Great Jones Distilling Company crafts some superb spirits, and key among them is its Straight Bourbon. No gimmicks, no tricks, just an understated art deco decorated bottle containing well-crafted, small-batch bourbon that clearly carries all of the knowledge of centuries of bourbon-making know-how.

Great Jones Straight Bourbon plays with classic flavors in artful ways. You'll find plenty of buttery caramel, rich vanilla, and oaky flavor in each sip. There's also more than a touch of brown sugar to take the sting off and make this offering a simple, sipping bourbon to enjoy on a hot summer's day. Great Jones Straight Bourbon is exactly what a premium bourbon ought to be: Unpretentious and true to form.

W.L. Weller 12 Year

Frankfort, Kentucky's Buffalo Trace Distillery's W.L. Weller 12 Year is a hearty but buoyant wheated bourbon combining the classic velvety smoothness of bourbon with a rich, mature taste. It's balance in a bottle, dark honey-colored, and full of complementary flavors. Bourbon lovers will be delighted to find some standard notes lingering inside, like vanilla and oak, but there's an unexpected hint of almond and a sweet, summery corn taste as well.

According to Breaking Bourbon, the savvy drinker will pick up on some fruity notes mingling with the sweeter flavors. W.L. Weller 12 Year has a tremendous body, too. Pour it into a Glenlivet glass, swirl it around, and you'll see some fabulous legs on the drink. This robustness complements the more nuanced flavors, so W.L. Weller 12 Year is neither overpowering nor underwhelming. Instead, it hits the sweet spot, and once you sip it, you'll want to have a bottle in your home bar at all times.

Booker's Bourbon Ronnie's Batch

According to Booker's Bourbon, this small-batch blend is a subsidiary of whiskey behemoth Jim Beam and is a premium, unfiltered bourbon with a lot of character and profound intensity. Aged and pure, Booker's Bourbon is one of Kentucky's greatest offerings, an unabashedly strong draught full of bold bourbon flavors designed to appeal to true aficionados. As Whiskey Wash points out, Booker's Bourbon Ronnie's Batch pays homage to longtime employee and warehouse manager Ronnie.

It's a fitting tribute with an impressive 124-proof intensity aged approximately seven years. Booker's Bourbon Ronnie's Batch is warm and inviting, with tons of creamy vanilla laced throughout the nose and each sip, plus spice accents here and there to complement the basic flavor palates. It's pleasant but potent, a bourbon without bells and whistles that relies entirely on technique and aging. There are no shortcuts with this one, and if you appreciate the bourbon-making craft, you'll love a rocks glass of Booker's Bourbon Ronnie's Batch.

Old Forester 150th Anniversary Bourbon

Another Kentucky gem, Old Forester's 150th Anniversary Bourbon, is a fierce, memorable drink full of intense flavors like tobacco and chocolate. It's also got a nice finish with bubbly cherry coca-cola and stone fruit (via Bourbon Banter). The crowning jewel is candied orange, which offsets the stronger flavors and renders this bourbon drinkable and balanced. Old Forester definitely took a well-calculated gamble on this bourbon, and it paid off marvelously.

Old Forester's 150th Anniversary Bourbon is satiny smooth, and despite its bevy of different flavors, it's never cloying and doesn't burn going down. You'll get each glorious bit of nuance without any whiskey pain, which is a massive plus for a big, bold bourbon like 150th Anniversary Bourbon. According to PR News Wire, consistency and quality are key to this bourbon's success. You can taste the craft in every sip, which makes this drink a winner in any book.

Wild Turkey's Russell's Reserve

Wild Turkey Bourbon is one of Kentucky's legacy distillers, but if you've never tried its premium offerings, you're in for a real treat. According to the Robb Report, Wild Turkey's Russell's Reserve is a super clear, ultra-filtered whisky that's a clean, crisp, satisfying sip. It's straightforward and unapologetic, precisely what a bourbon should be. It's silky with a good body and solid mouthfeel tinged with fruit, spice, and a bit of woodiness. Perceptive drinkers might pick up on the pepper, grapefruit, and herbaceous heft near the end of the sip.

What's surprising about Russell's Reserve is that its cornucopia of fruit flavor tends to skew a bit tropical (via the Robb Report), an exciting choice that plays well with more familiar oaky, vanilla, and caramel flavors. Enjoy this drink on chilled whiskey rocks for a refined taste that allows you to enjoy the bourbon ice cold without residual water.

Black Maple Hill 16-Year-Old Small Batch

Black Maple Hill is unique because, unlike the other faves on our list, it's not a brick-and-mortar distillery. Instead, it's a premium label reserved for cask-aged spirits that hit a particular quality bar. Crack open a bottle, and you'll immediately know that you've tapped into the good stuff. The nose is potent but not overwhelming, with warm, grainy notes, autumnal fruits, and plenty of balanced spice. The taste is rich and leathery, and it's as smooth as satin, thanks to 16 years of aging (via Distiller).

Black Maple Hill 16-Year-Old Small Batch benefits from a very clear and powerful flavor profile. With nuttiness, rich apples, molasses, brown sugar, and fall spices, it's like a small shot of October in a glass. So if you're looking for a statement-making bourbon and love your spirits unadulterated, cold, and straight, reach for this bottle. It will warm your insides, please your palate, and leave you with a brand new appreciation for bourbon.

A.H. Hirsch Reserve

Hirsch Whiskey proves that you don't have to be from the deep south to produce some darn fine whiskeys and bourbons. This San Francisco-based distillery makes modern classic magic with offerings like A.H. Hirsch Reserve, a straight bourbon packed with tasty caramel and vanilla with a few hints of pepper to entice the palate along the way. According to Drink Hacker, A.H. Hirsch Reserve relies heavily on the interplay of dessert flavors like butterscotch and vanilla and sprinkles some cherry, gingerbread, and even eucalyptus through the mix. If it all sounds off-the-wall, it's because the flavors don't seem like they should work together, but they definitely do.

According to Bev Net, A.H. Hirsch Reserve follows a long pattern and tradition for excellence and stellar spirit-making craft. It's one of the most expensive bottles of bourbon ever, but that price tag is more than fair and justified — since it won't be around forever.

Jefferson's Twin Oak Custom Barrel

Louisville Jefferson's Bourbon ages its Twin Oak Custom Barrel in a special barrel that infuses every drop of the drink with tons of rich oaky flavor, resulting in a very mature, sophisticated deep amber drink that's as silky as it is strong. You'll get a lot of the oak at first sniff, along with whiffs of apple, cinnamon, and butterscotch. There's a rich undertone of vanilla as well.

The body has a plethora of interesting and exciting flavors, like bright peppers, apples, and a little hint of almond. There's some oak in there, too, a nod to the maturation process and an overwhelming theme of this drink, according to the website. The Malt Review says Twin Oak Custom Barrel is reminiscent of a fresh slice of apple pie and has a lovely, but not overwhelming, hint of burn on the end. Not for the faint of heart but made for bourbon lovers, Twin Oak Custom Barrel is one to celebrate.

Pappy Van Winkle's Family Reserve 20 Year

Frankfort, Kentucky's Pappy Van Winkle's Family Reserve 20 Year comes in an understated, sepia-tinted bottle with an image of the family patriarch smoking a cigar. It sets the tone for the drink itself. If this bourbon was aged just one year longer, it would be able to buy a bottle of itself legally. Twenty years is a long, lovely maturation time, and you can taste the nuance in every sip of Pappy Van Winkle's Family Reserve 20 Year.

The color is robust, orange-tinged, and luxe. The bourbon shows its cards right away, with strong leather, coffee, and tobacco notes. There's a bit of vanilla in there, but unlike in sweeter, less mature bourbons, it's there as a supporting character, playing off the stronger mature notes for a perfect sip (via Whiskey Reviewer). Only newbies and bourbon blasphemers would dare mix this drink. Enjoy it straight, as Pappy Van Winkle would have intended.

Michter's Kentucky Straight Bourbon

Michter's, of Louisville, Kentucky, offers a no-nonsense, richly-tinged draught that speaks to the craft and is strictly for those who love and appreciate the nuance of good bourbon. Michter's Kentucky Straight Bourbon is a small batch blend with a floral and citrus nose that opens up reasonably quickly, revealing glorious hints of lime, geranium, and lemon (via Whiskey Rising). That's just the first trick that this devilish spirit has up its sleeve.

Expect musk and earthiness mingling with vegetal tastes and wood. It's not a sweet bourbon, nor is it really a mixing bourbon. Instead, if you prefer your poison robust and slightly bitter, it's the right bourbon for you (via Whiskey Rising). There is a touch of vanilla and anise and a delightful, surprising bit of toasty marshmallow near the end of the sip, but these are more complementary rather than center-stage notes.

1792 Full Proof

1792 Full Proof comes in a distinct, weighty bottle worthy of its contents — but even if it came in a plastic cup, it would still be one of the finest bourbons on the planet. According to the Lane Report, 1792 Full Proof is an awe-inspiring draught that took home 2020's Jim Murray's Whisky Bible Bourbon of the Year award, beating out heavyweights like Pappy Van Winkle for the crown. This bourbon is legendary because of its rich, smoke-infused taste that relies on the bourbon trifecta of earthiness, caramel, and vanilla to strike that sweet balance.

Although the tasting notes are reasonably ordinary, what's extraordinary is how perfectly they are blended. You'll get layers upon layers of smokiness and woodiness, shot through with luxe, melt-in-your-mouth caramel tones, and robust, sophisticated vanilla. There's absolutely nothing about this bourbon that tastes artificial or manufactured. Instead, it's high-quality and transcendental from start to finish.

Widow Jane The Vaults

Brooklyn's Widow Jane The Vaults is a mature, rare bourbon in a retro bottle with classic gold stenciling and a hand-printed batch number. The bottle is both innocuous and classy, perfect for the cosmopolitan at-home bartender, and what's inside is something extraordinary indeed. According to Widow Jane's website, The Vaults was designed to mimic hedonism in a glass, and it's easy to imagine the classic bottle with its amber gold at one of Jay Gatsby's famous bashes. It is indulgent, oak-aged, and velvety with spice, vegetal notes, and plenty of smoke.

Offsetting all of the robust notes is wintergreen, lemon, mint, and warm brown sugar. You'll get a pop of cherry at the end, a nice, round vanilla send-off, and a sprinkle of nutmeg for good measure. According to the Lane Report, there's some toasty coconut, chocolate, and caramel in there too. Knowledgeable bourbon drinkers might be able to pick up pecan and graham crackers running throughout as well.

Kentucky Owl Bourbon Batch #9

From Bardstown, Kentucky, Kentucky Owl is a boutique distillery that's developed something of a fanatic following (via Bev Net). Kentucky Owl Bourbon Batch #9 certainly has the fan base engaged, and this boozy bourbon hit delivers with a rollercoaster of different flavors all wrapped up in an old-time bottle that will look spectacular on your home bar. According to Bev Net, Kentucky Owl Bourbon Batch #9 taps into a sophisticated sweetness with notes of vanilla and juicy grape, as well as homestyle cinnamon rolls.

Thanks to a ribbon of honeysuckle running through each bottle, you'll also get some floral in there, accented perfectly by oak and caramel. It's a playful and fun blend that doesn't take itself too seriously but still shows off its expert chops with flavor pairing. So if you want a charming, slightly eccentric take on your typical bourbon, Kentucky Owl Bourbon Batch #9 is it.

Barrell Bourbon Batch 009

Louisville, Kentucky's Barrell Crafted Spirits is no stranger to expertly-blended draughts that make unconventional flavors sing (via Man of Many). Barrell Bourbon Batch 009 is yet another stellar example of the distillery's commitment to excellence in all things alcohol. Visually, the bottle is stunning, with a neutral but impactful label hand-lettered with the batch number and age. Inside, you'll find notes that skew slightly tropical, thanks to sweet plantains, quince, and luxurious notes of molasses and almond butter, according to the website.

As you sip, there's more in store, including surprising hints of s'more, apricot, and stone fruit. It all works together to set up a brilliant tapestry of sun-drenched tropical flavors that also pay homage to Barrell Bourbon's Kentucky roots with grounding leather and a bit of tea. Enjoy this spirit ice-cold, neat, or over whiskey rocks for maximum impact and taste, preferably on a lovely veranda looking out at the sunset.

Bulleit Barrel Strength

Kentucky's Bulleit Barrel Strength is a rye-heavy, award-winning blend that takes single barrel artistry to dazzling new levels. This distinct, copper-hued draught gets its punch from plenty of spice and the warm backdrop of oak. You'll taste plenty of wood and autumnal spices like nutmeg in each sip, and the taste lingers delightfully on your tongue, dancing with notes of buttery toffee and another hit of oakiness.

Bulleit Barrel Strength is incredibly creamy despite the robust play of flavors. In addition to the sweetness and woodiness, you could pick up some dried fruit notes lingering at different points of the sip. Expect heartier tastes of sweet and tart apple, citrus, and peach with a slight undertone of honey to wrap it all together. If you really know your stuff, you might even pick up some fennel mingling with the cinnamon on the back end.

Willett Family Estate Bottled Bourbon

Willett Family Estate Bottled Bourbon is one of the distillery's finest products, a nuanced and refined barrel-proof draught from the heart of Kentucky. According to Single Malt Savvy, Willett Family Estate Bottle Bourbon has a lot going on, but it's all balanced and beautiful, letting the product shine through in each sip. Start off with a sugary nose full of root beer, brown sugar, cherries, oranges, and chocolates. This sets the stage for the initial sip, heavy on the cinnamon but balanced by the vanilla and cherries. Pepper gives it an unexpected kick and rounds off the taste nicely.

A smoky finish concludes the drink, leaving some lingering sweetness, oakiness, and the pungent punch of pepper lingering long after you've swallowed it. With all of these flavors, you could expect Willett Family Estate Bottled Bourbon to be slightly over the top, but it's actually elegant, a huge feat for such a robust bourbon.

Woodford Reserve Kentucky Straight Bourbon

Woodford Reserve of Kentucky is a longtime distillery notable for its mature flavors, rich amber colors, and expert blends. Woodford Reserve Kentucky Straight Bourbon is the ultimate archetype of this style, a rich and woody blend spiked with spice, decadent florals, and plenty of fruit to brighten up the mix. With a stunning 200 flavors profile, it's big and bold without being cluttered, the sign of excellent distillation skills and an expert palate, according to the website.

Even if you don't pick up on all 200 of the flavor notes, you'll still enjoy the smooth and sophisticated ride that this bourbon takes you on. Beautiful all on its own, paired with steak, or splashed into an Old Fashioned, Woodford Reserve Kentucky Straight Bourbon is velvety, toasty, and accented with dessert notes like butterscotch, cocoa, and vanilla (via Master of Malt). Bev Net notes that savvy sippers could also catch some oatmeal cookie in the nose and dark chocolate in the body.

Watershed Bourbon

Watershed Distillery in Columbus, Ohio, makes a beautiful bourbon blend that's a brilliant fusion of three premium whiskeys. Meet Watershed Bourbon, a triple marriage of spirits brandy cask-aged and bursting with stone fruit, woodiness, and apple (via Vine Pair). While many bourbons cater specifically to bourbon enthusiasts, Watershed Bourbon is much more accessible, with a straightforward and successful blend of wood and fruit. It's light enough to enjoy neat, with a bit of water to open things up, or in a classic mixed drink.

Apple brandy cask aging lends this bourbon its trademark sweetness and lets it take on the twin qualities of the brandy and the succulent autumnal taste of apples. These base notes are only complemented with rich, dark stone fruits and a nice light ribbon of spice. If you're looking for a serviceable, high-end bourbon that will please both bourbon lovers and novices, reach for Watershed Bourbon.